1-[((E)-{2-[(2-Nitro­benz­yl)(2-{[(E)-(2-oxidonaphthalen-1-yl)methyl­idene]aza­nium­yl}eth­yl)amino]­eth­yl}aza­niumyl­idene)meth­yl]naphthalen-2-olate monohydrate

Saeid Menati; Hadi Amiri Rudbari; Reza Azadbakht; Giuseppe Bruno

doi:10.1107/S1600536811047465

. 2011 Nov 16;67(Pt 12):o3321. doi: 10.1107/S1600536811047465

1-[((E)-{2-[(2-Nitrobenzyl)(2-{[(E)-(2-oxidonaphthalen-1-yl)methylidene]azaniumyl}ethyl)amino]ethyl}azaniumylidene)methyl]naphthalen-2-olate monohydrate

Saeid Menati ^a,^*, Hadi Amiri Rudbari ^b, Reza Azadbakht ^c, Giuseppe Bruno ^b

PMCID: PMC3238971 PMID: 22199820

Abstract

The title Schiff base compound, C₃₃H₃₀N₄O₄·H₂O, adopts an E configuration with respect to each C=N double bond. In the molecule, there are naphthoxide anions and the protonated imino N atoms. Intramolecular N—H⋯O hydrogen bonds lead to the formation of approximately planar (maximum deviation 0.029 Å for H atom) six-membered rings.. In the crystal, molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds as well as C—H⋯O contacts, leading to the formation of a three-dimensional network.

Related literature

For related structures, see: Keypour et al. (2008 ▶); Zeng et al. (1999 ▶); McKee et al. (2006 ▶). For Schiff base derivatives incorporating a fluorescent moiety as tools for optical sensing of metal ions, see: Azadbakht et al. (2011 ▶).

Experimental

Crystal data

C₃₃H₃₀N₄O₄·H₂O
M _r = 564.63
Monoclinic,
a = 13.8808 (6) Å
b = 14.8951 (8) Å
c = 14.7517 (8) Å
β = 111.754 (2)°
V = 2832.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.5 × 0.3 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) ▶ T _min = 0.671, T _max = 0.745
27583 measured reflections
5261 independent reflections
3757 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.195
S = 1.04
5261 reflections
395 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047465/qm2040sup1.cif

e-67-o3321-sup1.cif^{(27.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047465/qm2040Isup2.hkl

e-67-o3321-Isup2.hkl^{(252.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811047465/qm2040Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.79 (3)	1.99 (3)	2.596 (3)	133 (3)
N3—H3⋯O1	0.84 (3)	1.88 (3)	2.567 (3)	138 (3)
O5—H5D⋯O1ⁱ	0.95 (4)	1.82 (4)	2.747 (3)	164 (5)
N2—H2⋯O4ⁱⁱ	0.79 (3)	2.60 (3)	3.183 (4)	131 (2)
O5—H5C⋯O2ⁱⁱⁱ	0.94 (3)	1.91 (3)	2.839 (3)	170 (3)
C1—H1A⋯O5^iv	0.97	2.53	3.409 (4)	151
C2—H2A⋯O5^iv	0.97	2.55	3.359 (4)	140

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

We are grateful to the Islamic Azad University of Khorramabad for financial support.

supplementary crystallographic information

Comment

Schiff bases (imines) are known to be good ligands for metal ions. A number of the Schiff bases have antitumor properties, antioxidative activities, attractive electronic and photophysical properties. In addition, Schiff base derivatives incorporating a fluorescent moiety are appealing tools for optical sensing of metal ions (Azadbakht et al. 2011). The title compound, (I), crystallizes in the Monoclinic space group P2(1)/c. Figure 1 shows the ORTEP representation of the molecule with thermal ellipsoids at the 30% probability level. In the compound, there are π-π interactions between the naphthalene moiety and the nitrobenzene moiety with the distance of 3.516 (3) Å. The structural features of I (The bond lengths) provides evidence for the existence of a naphthoxide anions and the protonated imino N atoms in the crystal structure of I that stabilize by intramolecular hydrogen bond between the naphtholate oxygen and the iminium nitrogen (O-···H—N+). This molecular conformation is determined by the formation of pairs of intramolecular N±–H···O– (1.888 (3) Å) hydrogen bonds. These interactions lead to the formation of six- membered rings (see scheme). Details of the hydrogen-bonding geometry are given in Table 1. Each of these hydrogen-bonded rings adopts a nearly planar conformation. In the six-membered rings, the maximum deviation from the mean planes is 0.029 Å for H (N±–H). The crystal packing in compound (1) is stabilized by O—H···O– interactions (Fig. 2 and Table 1).

Experimental

A solution of NaOH (3 mmol) in methanol (10 cm3) was added to a suspension of N1-(2-nitrobenzyl)-N1-(2-aminoethyl)ethane-1,2- diamine trihydrochloride (0.357 g, 1 mmol) in methanol (10 cm3). The mixture was stirred at room temperature for a few minutes then filtered, and the precipitate was washed well with methanol (10 cm3). The washings and the filtrate were combined and to this solution was added 2-hydroxy-1-naphthaldehyde (0.344 g, 2 mmol). After refluxing the solution for 8 h on cooling the product was recovered as a yellow powder, which was recrystallized from methanol.